Top 10 Grammy Winning Hip-Hop Songs: Ranked

Oct 18

By: Noah Weinberg

The Recording Academy, the slightly corrupt, “allegedly” racist organization that annually runs the well-known Grammy awards. Whether you love or hate the Grammys, the award show continues to hold an esteemed status in the music industry. The Grammys have crowned some of hip-hop’s best and worst with the iconic, coveted gilded gramophone. Unfortunately, throughout its checkered history, The Recording Academy has been astonishingly average at selecting the correct winners for their awards. A decade ago, Macklemore won a Grammy over Kendrick Lamar. And according to the Academy, Cardi B’s Invasion of Privacy is a superior album to either Travis Scott’s Astroworld or Pusha T’s Daytona. So with that being written, I found this list somewhat easy to compile. I tried to limit my rankings to one song per artist (with a few minor exceptions) to discuss as many legendary artists as possible. So without further ado, here are my top ten Grammy-winning rap songs.

10. Mama Said Knock You Out by LL Cool J

A quintessential relic of a bygone 90s boom-bap era, LL Cool J’s “Mama Said Knock You Out” remains one of the fiercest tracks ever to secure a Grammy award. Backed by a soulful vocal sample and harsh, percussive drums, LL ferociously enters the song with one of the hardest and most iconic opening lines in all of hip-hop:

“Don’t call it a comeback!”

It’s a timeless song filled to the brim with triumph and tenacity. LL used his grandmother’s words as inspiration, as she told him to “knock out” those that were disappointed with his previous album. That frustration towards his critics led to the most popular song of LL Cool J’s career, cementing the New York native as a household name.

9. Yeah! by Usher featuring Lil Jon and Ludacris

“Peace up, A-Town down”

That’s how Usher’s “Yeah!” begins, right before a bouncy eight-note crunk-inspired keyboard takes center stage of this smash single. “Yeah!” remains a cultural hit for the flawless blend of Usher’s RnB crooning and Lil Jon’s monstrously loud ad-libs. This track displayed such a seamless crossover of musical genres that Lil Jon coined the song as something entirely new, “crunk&B.” Every aspect of this grammy-winning song holds up, even Ludacris’ addition. Ludacris’ whimsical cadence and intonation within his guest verse give listeners an easy opportunity to rap along. Eighteen years later, you’ll still find all sorts of people mimicking the rapper’s unusual flow:

“Watch out, my outfit's ridiculous/In the club looking so conspicuous.”

Simply put, this 2004 banger is one for the ages. Whether at a party, club, barbeque, bar mitzvah, or quinceanera, it doesn’t appear that “Yeah!” will ever leave our delighted ears.

8. Bubblin by Anderson .Paak

If you’ve been living under a rock for the past eight years and don’t know who Anderson .Paak is, I kindly suggest that you…

1. Find a slightly more suitable living situation, preferably one that isn’t beneath hard stone.

2. Stop whatever you’re doing and lose yourself in the sheer glory that is Anderson .Paak’s discography because this man simply refuses to release a bad song.

“Bubblin” demonstrates the best rapping performance of Anderson’s career. With rapidly rapped lyrics and an elegantly boastful hook, this Grammy-winning single infuses the listener with an unwavering west-coast flare. Jahlil Beats, Antman Wonder, and .Paak himself composed this bumpy trap beat, and “Bubblin’s” euphoric instrumentation cements itself as a classic summer jam through the song’s deliriously delightful horn inflections. “Bubblin” may not be the most well-rounded Anderson .Paak song, but it’s still a terrifically gleeful track from one of the 2010s most dynamic artists.

7. Empire State of Mind by Jay Z featuring Alicia Keys

Honest question: Is there a better New York anthem than Jay-Z's “Empire State of Mind”? Between Alicia Keys’ jaw-dropping hook, a piano-led instrumental with harmonic rattling keys, and three perfectly penned Hov verses, this 2009 classic holds up in every aspect. Jay’s verses expertly blend personal recollection with universal adoration toward the city that raised him. Hov seamlessly mixes details of his drug dealing past with well-known New York references like Spike Lee, the Statue of Liberty, the Yankees, Knicks, Nets, and many more. “Empire State of Mind” was the first Jay-Z-led single to reach #1 on the Billboard Hot 100, fully establishing the Brooklyn rapper as an unequivocal mogul in the genre. Thirteen years later, “Empire State of Mind” is just as relevant, largely because the track contains a timeless message of hope and starry-eyed wonder.

6. Doo Wop (That Thing) by Lauryn Hill

It takes a special kind of song to bring a smile to your face upon first pressing play, yet “Doo Wop” by Ms. Lauryn Hill continuously does just that. This track’s production is flawless, as all musical elements collide to form a rich and flavorful sonic stew. From the song’s simple grand piano chords to its groovy bassline, soothing background vocals, and victorious horn section, finding another hip-hop instrumental at this level is quite challenging. That’s without even mentioning Lauryn Hill’s phenomenal singing and rapping. The Fugees rapper spends her breakout single warning both men and women not to be taken advantage of by the opposite sex for “that thing.” It’s a song that executes the difficult feat of being a conscious hip-hop song that's undeniably catchy and memorable. “Doo Wop” is a sonic display of Lauryn Hill at her best, as she casually demonstrates why she’s the rapper with the best singing voice (yes, even better than Drake).

5. Forgot About Dre by Dr. Dre featuring Eminem

A pure hip-hop song in every sense of the word, Dr. Dre and Eminem’s “Forgot About Dre” expertly showcases a master and protègè hitting on all cylinders. It should go without saying, but Dr. Dre’s production on this 2001 grammy-winning single is mesmerizing. The goosebump-inducing strings are stellar. The west-coast-influenced synths are perfectly placed and make this song feel all the more dynamic. Of course, that’s all without discussing the rapid-fire flows and braggadocious bars delivered by Dr. Dre and Eminem. Even though Eminem wrote the majority of lyrics on “Forgot About Dre,” Dr. Dre’s hunger and passion can easily be felt through his delivery, as he explains to his doubters that it’s nonsensical to believe that he “fell off.” Not to mention, this song contains a top-five Eminem verse of all time. Eminem’s signature high-speed flow, multisyllabic assonance, and top-notch wordplay are all thrust into the limelight here, with the Detroit rapper sounding as motivated as ever. Dre and Eminem’s best collaboration is on this list mainly because it’s an artifact of two hip-hop giants at the top of their game.

4. Family Ties by Baby Keem featuring Kendrick Lamar

Honestly, putting “Family Ties” as the fourth-best Grammy-winning rap song is a completely biased pick. It’s a song that’s only been out for a little over a year, but what can I say? I just can’t stop listening to “Family Ties.” Part of my adoration for the song has to do with the fact that I’ve seen Baby Keem perform it live five times in 2022 alone. And my goodness, this song just doesn’t allow itself to get stale. I erupt into a crazed frenzy whenever I hear those marching band trumpets. It doesn’t matter if my house is on fire and I must escape hastily. It doesn’t matter if my roommate has a sprained ankle and can’t make it out of our hypothetically burning home without my help. Once the opening horn motif of “Family Ties” begins, I will undoubtedly become entranced and take part in the sheer greatness that Baby Keem and Kendrick Lamar provide for the next four minutes and twelve seconds. I don’t have a single critique for this song. In fact, it’s simply “amazing, brother.”

3. N* in Paris by Kanye West and Jay Z

Has there been a more iconic opening line to a song since Will Ferrell’s snippet of “we’re gonna skate to one song, one song only” on 2011’s “N***** in Paris?” The short answer is no because following that brief distorted intro, Kanye West and Jay Z set one's eardrums ablaze with the greatest banger since the turn of the century. This show-stopping single situates Ye and Jay at their most confident and cocky. The rap duo finds themselves in Paris, and they can’t help but “ball so hard” so that “motherfuckers wanna fine” them. It’s an unabashedly flashy track with some of the most quotable lyrics in all of the 2010s. Jay Z can still explode an entire area with the line “Jackson, Tyson, Jordan, Game 6.” While Kanye West finds himself answering his age-old question “what she order?” with the now-famous response, “fish filet.” “N***** in Paris” is still the pinnacle of modern-day brag rap, as an ever-present pump-up song not likely to ever leave our party playlist.

2. Jesus Walks by Kanye West

Long before Mr. West was “balling so hard” with Jay Z in France, he was breaking new ground in hip-hop by being the first commercial rapper to spit bars about religion. “Jesus Walks” comes from Kanye West’s 2004 debut album, The College Dropout. With menacing vocal samples, thumping percussion, and some spectacularly impassioned rapping from Kanye, this song is a bonafide classic in the 21st-century musical pantheon. “Jesus Walks” was a bombshell release in the mid-2000s because no other pop song in recent memory was so fearlessly pro-Christianity. Kanye succinctly dissects the topic in his third verse when he raps:

“They say you can rap about anything except for Jesus/That means guns, sex, lies, videotape/But if I talk about God my record won't get played, huh?”

“Jesus Walks” might just be the most “Kanye West” song Kanye has made. It perfectly represents Ye’s bravery, recklessness, and authenticity toward a subject matter so closely tied to the controversial artist.

1. Alright by Kendrick Lamar

For my number one Grammy-winning rap song, I had to go with Kendrick Lamar’s “Alright,” arguably the most important and culturally impactful hip-hop record this century. “Alright” has taken on a life of its own outside of the context of Kendrick Lamar, as this groundbreaking trap-jazz fusion served as the central protest anthem for the 2015 Black Lives Matter movement. Few songs in American history can claim to be a beacon of hope and inspiration for protesters in the streets. Yet, Kendrick’s “Alright” has already joined the likes of “We Shall Overcome” and “The Times They Are A-Changin” as an all-time American protest song.

For a song that almost didn’t make it on Kendrick’s To Pimp A Butterfly, “Alright” contains everything one could possibly ask for in a hip-hop track. Pharrell’s production and chorus are dizzying and spine-tingling, as the world-renowned artist beautifully mixes hard-hitting 808 drums with smooth and seductive saxophone chords. Kendrick Lamar’s performance is unsurprisingly terrific because the Compton, CA rapper’s speedy delivery effortlessly floats atop the jazzy production. Despite numerous hardships and despair, Kendrick maintains a confident sentiment of optimism on “Alright.” Lamar reassures himself and the audience that even in the face of death, violence, and discrimination… “we gon’ be alright.” Kendrick’s “Alright” remains a culturally significant landmark in hip-hop, largely for its impact outside the genre. “Alright” is one of the most important songs to release this millennium, and it proudly wears the crown as the best Grammy-winning hip-hop song of all time.

Kyliah Almeida